Vacation rentals with a kayak in Madison County

River Front Mountain Views (Old Rag, SNP)

Relax with the whole family in this serene setting along a native brook trout stream where nature's sounds prevail. Most every room has wonderful views of the Hazel River and the Appalachian Mountains (Shenandoah NP) beyond. The river's clear waters invite fly fishing, and swimming holes abound as do nearby hiking trails in SNP (favorites, Old Rag and Marys Rock). Noted restaurants are nearby as are many vineyards and antique stores. (County code encourages multi-day [weekly/monthly] stays).

Firnew Cottage

A perfect family getaway from the city in the heart of Virginia Wine Country, 15 min from Shenandoah National Park, 30 min from Charlottesville. Private cottage on 265 acres with 3 mi. hiking trail, overlooks 2 ponds/playhouse offers complete farm experience. Walk to swimming hole on river, canoe/fish in lake, feed peacocks/ goats, collect fresh eggs. Great sunsets. Fire-pit. Close to wineries, breweries, Montpelier, Monticello - only 1.5 hrs to DC/Richmond. Pet friendly. Tour included.

Guest Cottage @ South River Farm

Escape to the serenity of South River Farm, nestled in the picturesque Virginia Piedmont. Only 15 min to Shenandoah National Park, our charming studio cottage boasts a luxurious king-sized bed, chic new furnishings, cozy en-suite bathroom, and state-of-the-art appliances, ensuring a relaxing stay. As our guest, revel in the expanse of our working farm: roam miles of bucolic trails, relax by a stocked pond (no license needed), or fish in our stocked trout stream. Welcome to your rural retreat!

Stone Bridge Farm - 5BR Historic Riverfront Estate

Step back in time—without giving up modern comfort. This fully renovated 5-bedroom estate, originally built in 1882, blends historic character with elevated design on 8 private acres and .1 mile of riverfront access. Thoughtfully restored and beautifully updated, this is a rare Virginia retreat ideal for families, wedding parties, retreats, and extended stays. With a thoughtfully designed ADA-accessible apartment, guests find space, privacy, and flexibility in a truly unforgettable setting.

Pondside Retreat w/ Fire Pit, Fishing & SNP

Wake up to pond views just 15 minutes from Shenandoah National Park. Stroll 6+ private acres, cast a line, or sip coffee as deer wander nearby What you’ll love: 🛌 4 roomy bedrooms, 8 beds—ideal for families & groups 🔥 Fire pit on serene patio overlooking the pond 👨🏻‍🍳 Fully stocked kitchen & grill ✨Fast Wi-Fi + workspace After a day of hitting the trails and sipping wine, gather for games in the great-room, then fall asleep to frog songs across the water. Book your relaxing stay today!

Stone Bridge Farm - 1 BR Riverfront ADA Apartment

This private apartment is part of a historic 1882 riverfront estate, offering comfort, accessibility, and peaceful surroundings. Ideal for solo travelers, couples, extended stays, or guests attending events nearby who want independence and ease of access. * Private entrance and parking * Kitchenette and sitting area * Designed to meet most ADA guidelines * Accessible bedroom, kitchenette and bathroom with transfer shower chair available * Quiet, private setting within a larger estate

Home with beautiful mountain and river views

Welcome to the Madison House! This custom designed and built estate rests on a knoll overlooking 13.5 private acres on the Robinson River in rural Madison County, VA. Views of the Blue Ridge Mountains and direct Robinson River frontage makes this property a perfect destination for all four seasons. The outdoor space is ideal for friends and family gatherings and is ideally located near restaurants, wineries and breweries. The indoor space is both spacious and cozy for ample relaxing.

The Skyhouse- simple & serene w/mountain views

Enjoy the solace and beauty of the Blue Ridge Mountains with modern and local comforts. Retreat and explore on this old 100acre farm- via foot- or float on the tiny pond in a kayak or SUP. Or venture out to Shenandoah National Park, the local coffee shops, eateries, wineries, and breweries. Whatever you choose the skyhouse is stocked with roasted coffee, farm-fresh eggs, fresh-baked bread, teas and soaps from our incredible local homesteaders and artisans.

White Oak glamp tent #4. Safari tent, on a deck!

Come hike White Oak Canyon and then stargaze at the Big Dipper Ranch. Spend your whole time on our 23 acres or use it as home base as you explore all that Madison County has to offer. Old Rag and White Oak Canyon are minutes away as are wineries, breweries, orchards and much more. Critters big and small, we have them all! Please know we are in a remote area and wild animals and insects are part of nature and come with the camping experience!

Glamping the "Powhatan" Tent #3

Glamping tent in large field surrounded by woods. Fire pit available. Composting toilet. Swimming/Fishing pond on property with trails through private woods. Close to Old Rag and White Oak Canyon trail heads. Wineries and breweries nearby. Social Distancing in the Shenandoahs! Critters big and small, we have them all! Please know we are in a remote area and wild animals and insects are part of nature and come with the camping experience!

Glamping The "Virginia" tent #1

Glamping tent in large field surrounded by woods. Fire pit available. Composting toilet. Swimming/Fishing pond on property with trails through private woods. Close to Old Rag and White Oak Canyon trail heads. Wineries and breweries nearby. Social Distancing in the Shenandoahs! Critters big and small, we have them all! Please know we are in a remote area and wild animals and insects are part of nature and come with the camping experience!

Glamp in style at Tent #2 "Mid Century"

Come stargaze at the Big Dipper Ranch. Spend your whole time on our 23 acres or use it as home base as you explore all that Madison County has to offer. Old Rag and White Oak Canyon are minutes away as are wineries, breweries, orchards and much more! Critters big and small, we have them all! Please know we are in a remote area and wild animals and insects are part of nature and come with the camping experience!